EP0140154A2 - 1,2,4-Triazolylpropanols, leur préparation et usage - Google Patents

1,2,4-Triazolylpropanols, leur préparation et usage Download PDF

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Publication number
EP0140154A2
EP0140154A2 EP84111417A EP84111417A EP0140154A2 EP 0140154 A2 EP0140154 A2 EP 0140154A2 EP 84111417 A EP84111417 A EP 84111417A EP 84111417 A EP84111417 A EP 84111417A EP 0140154 A2 EP0140154 A2 EP 0140154A2
Authority
EP
European Patent Office
Prior art keywords
formula
compound
alkali metal
triazolylpropanol
acid addition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP84111417A
Other languages
German (de)
English (en)
Other versions
EP0140154A3 (en
EP0140154B1 (fr
Inventor
Ikutaro Saji
Renzo Ohuchi
Katsuaki Ichise
Tomoharu Tanio
Takao Okuda
Toshio Atsumi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP58178914A external-priority patent/JPS6069071A/ja
Priority claimed from JP59177956A external-priority patent/JPS60136570A/ja
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to AT84111417T priority Critical patent/ATE40885T1/de
Publication of EP0140154A2 publication Critical patent/EP0140154A2/fr
Publication of EP0140154A3 publication Critical patent/EP0140154A3/en
Application granted granted Critical
Publication of EP0140154B1 publication Critical patent/EP0140154B1/fr
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the 1,2,4-triazolylpropanols (I) may be produced by either one of the following procedures: wherein M 1 is an alkali metal atom (e.g. sodium, potassium, lithium) and,R is as defined above.
  • M 1 is an alkali metal atom (e.g. sodium, potassium, lithium) and,R is as defined above.
  • the ketone compound (V) (U.S. patent 4,128,581) is first reacted with the dimethyloxosulfonium methylide (VI), and the resultant sulfide compound (VII) is then reacted with an alkali metal salt of the 1,2,4-triazole (VIII) to give the sulfide compound (IV), which is oxidized to the 1,2,4-triazolylpropanol (I).
  • the reaction between the ketone compound (V) and the dimethyloxosulfonium methylide (VI) may be effected in an inert solvent (e.g. dimethylsulfoxide) at a temperature of 30 to 60°C.
  • the amount of the dimethyloxosulfonium methylide (VI) is usually from 1 to 5 equivalents, preferably from 1 to 2 equivalents, to the ketone compound ( V ).
  • Antifungal activity test in vivo:-Candida albicans KB-8 as pre-cultured at 30°C for 4 days was suspended in physiologically saline solution, and the suspension was intravenously injected into DDY strain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP19840111417 1983-09-26 1984-09-25 1,2,4-Triazolylpropanols, leur préparation et usage Expired EP0140154B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT84111417T ATE40885T1 (de) 1983-09-26 1984-09-25 1,2,4-triazolylpropanole, ihre herstellung und verwendung.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP58178914A JPS6069071A (ja) 1983-09-26 1983-09-26 Ν−置換−１，２，４−トリアゾ−ル類
JP178914/83 1983-09-26
JP59177956A JPS60136570A (ja) 1984-08-27 1984-08-27 １，２，４−トリアゾリルプロパノ−ル類
JP177956/84 1984-08-27

Publications (3)

Publication Number Publication Date
EP0140154A2 true EP0140154A2 (fr) 1985-05-08
EP0140154A3 EP0140154A3 (en) 1986-12-10
EP0140154B1 EP0140154B1 (fr) 1989-02-22

Family

ID=26498303

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19840111417 Expired EP0140154B1 (fr) 1983-09-26 1984-09-25 1,2,4-Triazolylpropanols, leur préparation et usage

Country Status (5)

Country Link
EP (1) EP0140154B1 (fr)
AU (1) AU572889B2 (fr)
CA (1) CA1232909A (fr)
DE (1) DE3476800D1 (fr)
ES (1) ES8603434A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5159089A (en) * 1989-08-28 1992-10-27 Sumitomo Pharmaceuticals Company, Limited Selective production of threo-epoxy compounds
US5869512A (en) * 1996-02-28 1999-02-09 Zambon Group S.P.A Azole compounds with antimycotic activity for human and veterinary use
EP0927719A1 (fr) * 1997-12-26 1999-07-07 SSP Co., Ltd. Dérivés de triazole et leurs sels, leurs procédés de préparation et compositions pharmaceutiques les contenant
EP0933368A1 (fr) * 1998-02-02 1999-08-04 SSP Co., Ltd. Dérivés de triazole ou leurs sels à activité antimycotique,procédé de préparation et et composition pharmaceutique le contenant
US5977152A (en) * 1995-04-06 1999-11-02 Sankyo Company, Limited Triazole antifungal agent

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2928768A1 (de) * 1979-07-17 1981-02-12 Bayer Ag 1-(2,4-dichlorphenyl)-1-(2,6- dihalogenbenzylmercapto)-2-(1,2,4- triazol-1-yl)-ethane, verfahren zu ihrer herstellung und ihre verwendung als fungizide
NZ198085A (en) * 1980-08-18 1985-09-13 Ici Plc Regulation of plant growth with certain 2,2-di(hydrocarbyl)-1-(1,2,4-triazol-1-yl)ethan-2-ols
EP0061835B1 (fr) * 1981-03-18 1989-02-01 Imperial Chemical Industries Plc Composés de triazole , procédé pour leur préparation, leur utilisation comme fongicides de plantes et leurs compositions fongicides
CA1179678A (fr) * 1981-03-27 1984-12-18 Elmar Sturm Derive de triazole microbicide
GR78218B (fr) * 1981-07-02 1984-09-26 Ciba Geigy Ag
DK161382C (da) * 1982-04-01 1991-12-09 Pfizer Fremgangsmaade til fremstilling af 1,2,4-triazol-forbindelser eller farmaceutisk acceptable syreadditionssalte deraf
JPS58203973A (ja) * 1982-05-24 1983-11-28 Sumitomo Chem Co Ltd 光学活性なイミダゾリルアルコ−ル誘導体およびその製造法

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5159089A (en) * 1989-08-28 1992-10-27 Sumitomo Pharmaceuticals Company, Limited Selective production of threo-epoxy compounds
US6306880B1 (en) 1995-04-06 2001-10-23 Sankyo Company, Limited Triazole antifungal agent
US6300357B1 (en) 1995-04-06 2001-10-09 Sankyo Company, Limited Triazole antifungal agent
US5977152A (en) * 1995-04-06 1999-11-02 Sankyo Company, Limited Triazole antifungal agent
US5869512A (en) * 1996-02-28 1999-02-09 Zambon Group S.P.A Azole compounds with antimycotic activity for human and veterinary use
US6194592B1 (en) 1997-12-26 2001-02-27 Ssp Co., Ltd. Triazole derivative or salt thereof, preparation process thereof and pharmaceutical containing said compound as an effective ingredient
US6083968A (en) * 1997-12-26 2000-07-04 Ssp Co., Ltd. Triazole derivative or salt thereof, preparation process thereof and pharmaceutical containing said compound as an effective ingredient
US6204415B1 (en) 1997-12-26 2001-03-20 Ssp Co., Ltd. Triazole derivative or salt thereof, preparation process thereof and pharmaceutical containing said compound as an effective ingredient
EP0927719A1 (fr) * 1997-12-26 1999-07-07 SSP Co., Ltd. Dérivés de triazole et leurs sels, leurs procédés de préparation et compositions pharmaceutiques les contenant
US6172266B1 (en) 1998-02-02 2001-01-09 Ssp Co., Ltd. Triazole derivative or slat thereof, preparation process thereof and pharmaceutical containing said compound as an effective ingredient
US6184396B1 (en) 1998-02-02 2001-02-06 Ssp Co., Ltd. Triazole derivative or salt thereof, preparation process thereof and pharmaceutical containing said compound as an effective ingredient
US6040325A (en) * 1998-02-02 2000-03-21 Ssp Co., Ltd. Triazole derivative or salt thereof preparation process thereof, and pharmaceutical containing said compound as an effective ingredient
EP0933368A1 (fr) * 1998-02-02 1999-08-04 SSP Co., Ltd. Dérivés de triazole ou leurs sels à activité antimycotique,procédé de préparation et et composition pharmaceutique le contenant

Also Published As

Publication number Publication date
ES536227A0 (es) 1985-12-16
AU572889B2 (en) 1988-05-19
AU3294484A (en) 1985-04-04
DE3476800D1 (en) 1989-03-30
EP0140154A3 (en) 1986-12-10
ES8603434A1 (es) 1985-12-16
EP0140154B1 (fr) 1989-02-22
CA1232909A (fr) 1988-02-16

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